Issue 46, 2013

Synthesis of rac-Lindenene via a thermally induced cyclopropanation reaction

Abstract

The first synthesis of the sesquiterpene Lindenene is described. A novel non-catalysed intramolecular cyclopropanation reaction between a diazoketone and an unactivated alkene was utilised to construct the relatively labile ketone precursor with complete stereocontrol. This ketone was transformed in three steps into Lindenene.

Graphical abstract: Synthesis of rac-Lindenene via a thermally induced cyclopropanation reaction

Supplementary files

Article information

Article type
Communication
Submitted
22 Aug 2013
Accepted
11 Oct 2013
First published
11 Oct 2013

Org. Biomol. Chem., 2013,11, 8026-8029

Synthesis of rac-Lindenene via a thermally induced cyclopropanation reaction

T. W. Fenlon, M. W. Jones, R. M. Adlington and V. Lee, Org. Biomol. Chem., 2013, 11, 8026 DOI: 10.1039/C3OB41716F

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